Silver Bay

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Bathtub

Hair Dryer

Toiletries

Bathroom

Freezer

Espresso Machine

Pod Coffee Machine

Fridge

Oven

Stove

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

High Chair

Kitchen & Dining

Iron

Ironing Board

Hangers

Washing Machine

Dryer

Bedroom & Laundry

Swimming Pool

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Fireplace

Central Heating

Heating & Cooling

Parking Available

Free Parking On Premises

Free Parking On Street

Private Entrance

Parking & Access

Balcony

Garden

Outdoor

Smoke Detector

Carbon Monoxide Detector

First Aid Kit

Fire Extinguisher

Other

Once an 1890s carriage house, this home has been designed for country living for a small family. Low timber ceilings and hardwood floors retain the barn-like element, but instead of hay bales, you’ve got comfortable king-size beds for grown-ups and secret sleeping spots for kids in the mezzanine above the loft. Huge windows in the living room let in the sunshine, streaming through the trees, and in the evening, there’s a wood-burning stove to keep the chill at bay. The open-plan kitchen has a large double fridge, kitchen island and plenty of storage space for all the fresh goodies from the nearby farmer’s market. You’re in the middle of nature’s bounty here, after all. The farm is at the foot of the Catskills, away from it all, so you can spend your days immersed in the wilderness of hiking and biking trails. Stick close to home and wander the acres of farm grounds, through woodlands, past ponds or just the short dander to the farm’s swimming pool.    

Old Macdonald

Library of Books

Sonos

Board Games

Satellite / Cable TV

Sound System

Piano

Entertainment

Dishwasher

Microwave

Toaster

Kettle

Blender

Extra Pillows and Blankets

Cleaning Products

Black-Out Blinds

Desk / Workplace

Air Conditioning

Self Check-in / Check-out

Barbeque

Outdoor Fireplace / Firepit

Outdoor Seating

Sun Loungers / Beach Chairs

Throws

Welcome Hamper

Nice to haves

Pets Allowed

Pets

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice. This place is made for taking it back to analogue and spending quality time together, around the stand-up piano, playing a board game in the sunny second sitting room, or pausing for a moment in the secret reading nook. A low, wooden ceiling, exposed brick wall and a wood-burning stove in the main lounge provide the ‘cosy’, while the plush velvet armchairs and antique dining table provide the ‘divine’. The bistro seating in the kitchen comes with a view of Butternut Mountain. Plus, there are several laptop-friendly desks designed for remote working and a dedicated office for video calls.

Outside, (well, almost outside) you’ve got an enclosed front porch with deck chairs for sunny days and a first-floor balcony begging for an evening tipple. In the surrounding greenery of the garden, let the kids run free on the lawn before gathering the group around the fire pit for a spot of stargazing at night.

You’re a five-minute drive from the artisan shops, local markets and restaurants of Great Barrington here, and skiing on Butternut Mountain is a short drive away too. 

Divine Inspiration

Hot Tub

Sauna

EV Charger

Balcony / Patio

Hammock

Patio / Terrace

Sitting alongside an enchanting creek, this cabin is a tranquil haven with a lot to offer. From the hot tub and wood fired sauna to the beautiful views, this is the perfect setting for a refreshing and romantic retreat. There’s also a barbecue, a pizza oven and a fire pit for magical night’s under the stars. Inside, the rooms are just as welcoming thanks to the cosy living room with a fire, the serene bedroom and the games room. Well behaved pets are welcome and you’ll find plenty to explore in the area. Follow nearby trails, discover charming towns and explore Lake Colgate and Hunter Mountain. 

The Creekside Cabin

Netflix

Record Player

Smart TV

Luxury Toiletries

Cafetiere

Ceiling Fans

Multiple Sets of Keys

Child Friendly

Fill your lungs with the scent of freshly chopped firewood as you step from the crisp Catskills mountain air into this gabled-roofed cottage. Whether you're a couple seeking stolen moments or a group of friends in search of calm, you'll find what you're looking for here. 

The wood-heady interiors cater to those in love with old-school design, particularly with the vintage wood-burning stove, record player and accompanying vinyl collection. On sunny days, a curl up on the hammock and listen to the babbling brook for hours on end – this simple pleasure is surely a tonic for the soul.

Keen hikers will no doubt be drawn to the nearby trails, taking you through the Catskill Mountains with the promise of spectacular vistas along the way. The town of Woodstock, made famous by the iconic 1969 music festival, is just a forty-minute drive away. Here you can load up on supplies and enjoy a hearty meal before heading back to your country retreat.

Cottontail Creek

Cot / Crib

Breakfast Included

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops. Perfect for a cosy couple or a small family, this home can welcome up to four guests, though two of them will have to sleep on the sofa bed. Spend your time reading on the porch, playing lawn games, and hiking in the area, before coming home to whip up a delicious meal in the fully equipped kitchen and settling down for a great night’s sleep in the King bed. Thanks to its picturesque setting, The Great Frontier is the ultimate escape for those who want to unwind and recharge in the comfort of nature.

The Great Frontier

Children's Dinnerware

Trash Compactor

Drying Rack

Access to Beach

Beach / Pool Towels

Beach Essentials

Security Cameras

Sitting peacefully on the edge of North Twin Lakes, this stylish cottage sets the tone for a restorative retreat in Livingston. Featuring beautiful views, calm rooms and a range of personal touches, you’ll find everything you could need to disconnect and embrace the natural elements. Complimentary toiletries are provided and children’s amenities are available on request, plus there are plenty of entertainment options – including board games, Bluetooth Speakers, Smart TVs and three kayaks. Outside, you’ll find a private beach, a fire pit and easy access to the nearest amenities. 

Lake of Beauty

Amazon Prime

Streaming Services

Baby Bath

Bathrobes

Rain Shower

Vacuum Cleaner

Desk

Workplace

Temperature Control

Underfloor Heating

Outdoor Audio

Outdoor Kitchen

Mosquito Net

Stair Gates

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home. It was proudly featured in Italy's Icon Design Magazine for its attention to detail and considered use of elegant and characterful materials. 

We loved the living space, particularly the expansive ceilings, enormous windows and integration of concrete and wood. Rise and shine to picturesque views of the beautiful garden. Relax on the outdoor day bed, which looks out over the legendary Indian Head mountain ridge, have a picnic by the swimming pond, surrounded by juniper trees and century-old cedars, or follow the burbling stream into the woods. Then later, gather around the fire pit. Whatever you decide to do, this home invites you to slow down the pace in style.

If you'd like to explore further afield, lace-up your boots and take a drive out to a hiking trail  –  the Indian Head Wilderness and the Bluestone Wild Forest are no more than fifteen minutes away. 



The Pond House

This beautiful old clapboard church has been turned into a woodland retreat like no other, where deer regularly stroll among the trees. Just outside Woodstock, there are craft beer breweries, farm shops and mom and pop coffee shops a short drive away, and trails into the Catskills are all around. From the outside, this home still looks like it holds Sunday Service, tucked in 1.5 acres of forest. 
Arched, stained-glass windows throw rainbows of light into the living room and what was once the altar is now a cosy nook for a wood-burning stove, framed by the wooden mantel from a famous Broadway theatre. The kitchen is fully-equipped with spices, ingredients, utensils and everything you'll need to prepare a hearty home-cooked meal. What was once the Sunday School room is now a lavish bedroom and just beneath the belltower, you’ll find a reading nook for lazy days, plus a range of games to keep everyone entertained. Outside, you’ll find a barbecue grill and seating on the patio, and a hammock to enjoy the sounds of the forest with a gentle sway. This is one home that really needs to be seen to be believed. 
Woodstock STR Permit No: 21N239

Woodland Hymnal

Home Cinema Setup

DVD Player

DVD Library

Projector

Mini Bar

Wine Cooler

Private Pool

Electricity Adaptors

Step-Free Access

Herb Garden

Umbrellas

This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day. Inside, it feels incredibly warm and welcoming, making it perfect for family gatherings and spending time with your loved ones. The screened porch was extremely inviting, it’s the kind of place that inspires you to slow down. While there’s a lot to love about this home, we couldn’t get enough of the garden – manicured and green, it also boasts an infinity pool.

Jewel on the Hudson

Baby Monitor

Bicycles

Heated Pool

Buzzer / Wireless Intercom

Single-Level Home

Urbanites looking for a tranquil getaway will enjoy the large indoor and outdoor spaces to relax and unwind. Each room has been lovingly styled by the host, Ayanna, who has instilled her character and charm into the home. The location has a semi-rural feel, which is wonderfully peaceful, but The Archway is still located near to the village centre. The home is well suited for families as there's lots of room for children to play and the twin bedroom has been thoughtfully designed to welcome young ones. 

The Archway

Luxury Bedding

Have you ever wanted your very own slice of the Catskills? Of course, you have. Well, here's ten acres of it, to be precise. And it all comes with riverside deckchairs, a six-person hot tub, dense woods, and tubes for floating down the river. It's also safe to say that from this Big Indian Victorian manor, you'll have plenty of stellar hiking and ski resorts within a thirty-minute drive. Not to mention the Peekamoose Restaurant – just one minute away for moments when you don't feel like cooking. Of course, if you want to whip up your own culinary masterpiece, you'll have your enormous kitchen opening onto the outdoor deck, for leisurely riverside dinners too. Your host – a New York-based designer – has crafted the interiors to his idiosyncratic taste, so you'll find that the thoughtful touches such as Moroccan tiles, high-end bedding and paintings by local artists offer an unforgettable experience worth writing home about. So set off on endeavours into the private forest land – there's no better place to go on an adventure amidst nature in the Big Indian wilderness than here. Plus when you're ready to curl up at the day's end, there are plenty of snuggly spots to get cosy, whether that's inside the house, where you can make the most of the endless streaming options available from Netflix, Hulu, Amazon and HBO. Or, if you'd rather spend your evenings in the great outdoors, gather around the fire pit with a cup of hot cocoa – ready to roast some smores. 

Which Way The River

Tucked neatly at the border of the Catskills, this chalet in Lake Hill is an idyllic home for those seeking an alpine retreat. With Cooper Lake and the Mink Hollow hiking trail nearby, it’s effortless to reconnect with nature here. Back at home, this modern cabin considers your every need after a day out in Woodstock, just four miles away. There’s a hammock, sound system, record player and fire pit for cosy nights at home. And while the lofted bedrooms aren’t so private, there’s plenty of space for a couple of friends to spend quality time.

Hearthside Haven

Sweetwater Hideaway is a magnificently organic cabin nestled in the forestry Woodstock landscape.  The timber vaulted ceiling, exposed wooden beams and deep chestnut finishings create a grand interior. Inviting sofas set around a stone-walled fireplace and a quaint library nook add a homely, cosy element to the house that is furthered by the wonderfully rustic kitchen. Simple, elegant bedrooms have plush beds and plentiful dressing room, including one organically-inspired room and a bright, colorful dedicated children’s room. There are luxurious bathrooms that have exquisitely tiled walk-in showers and soaking tubs. The cabin is nestled into the beautiful natural outdoors, while also being near enough to Woodstock to wander through legendary town. Just take a short drive to the town centre to explore all the shops and restaurants there are, or perhaps head to the Overlook Mountain Trailhead for a wholesome day of hiking. 

Sweetwater Hideaway

The Ashokan is an exquisite barn-styled house nestled within rich woodland landscape. The quaint exterior shelters an incredibly contemporary and stylish interior. From the patterned floors and wonderful impressionist paintings, to the rustic oak furnishings and floorboards, this house seamlessly blends homeliness with elegance. The large bedrooms have plush deluxe beds (although the mezzanine bedroom offers very little privacy and has no curtains), as well as plentiful dressing space and luxurious bathrooms. The estate is located moments away from the beautiful Ashokan reservoir. Spend your days taking in the breathtaking landscape while hiking the trails, or perhaps head into the nearby Woodstock to wander around the legendary town. 

The Ashokan

Private Parking

Surrounded by acres of forest, flowing streams, waterfalls and historic ruins, this little cottage welcomes you to experience the natural beauty of the Berkshire mountains. 

Located within a former Shaker settlement, there’s an abundance of charm and character here. From the antiques and art to the snug furnishings and personal touches, the owners have designed this space to enrich your stay with warmth and ease. So whether you’re here for an adventurous escape or for total relaxation, this home welcomes you to enjoy it all in the heart of New Lebanon.

Snuggle up in front of the fire, get cosy with a book, admire the views and gather for heartwarming evenings around the kitchen table. However you spend your time here, every moment promises to be enhanced by the unique spirit of this location. 

From here, it’s just a five-minute drive to the restaurants, shops and antique stores of New Lebanon. And for explorations further afield, you’ll find easy access to the charming villages of New England as well as the Hudson Valley.

A Little Love Note

Explore ten acres of lush, green land at this cosy ranch, which lies just eight miles from the historic town of Windham. From its perch high up on a hill, you’ll have incredible views of the rolling fields down below. Watch the sun set over the Catskills mountains from the fire pit, or enjoy an al fresco meal on the deck, admiring the beautiful autumnal colours of the trees if you visit in fall. Inside, enjoy meals around the sociable dining room table, which boasts views of the countryside. On cooler evenings, sink into the sofas in the comfortable living room and warm up in front of the wood-burning fireplace.

Autumnal Colours

Ice Machine

Juicer

Rice Maker

Private Washing Machine

Private Dryer

Laundry Supplies

Accessible Parking

Free Parking

Early / Late Check-Out Available

Safety Gates

When you want to get away from the hustle and bustle, this New Lebanon home is the perfect choice. You’ll not only leave the hectic city behind – stepping through the doors feels a little like stepping back in time. 

This home is 150 years old, and was a Shaker workshop. It’s on the National Registry of Historic Places and has been beautifully renovated to emphasise its history. You’ll find Shaker details like wide board pine floors, and the paint colours used are all accurate to the era. The history of a former Shaker settlement is evident at every turn, but modern convenience has also been considered. Everything you might wish for has been taken care of, so your stay will be comfortable as can be. 

The home is stunning. Elegance and historic charm come together in every stylistic detail. There’s plenty of room for everyone to gather together, whether it’s for elaborate meals prepared in the attractive kitchen, or around the fire pit for marshmallows and spooky stories. 

You can look forward to mesmerising views of the Lebanon Valley, and can explore the area on foot. There’s a forest and meadow that are ideal for hiking, as well as a nearby pond and waterfall to visit. The remoteness makes this a wonderful base for a relaxing stay. Though when you feel adventure calling, you can easily answer by driving to Berkshire and the Hudson Valley, where you’ll find plenty of restaurants, shops, and theatres. 


Ode to the Past

A grand townhouse in the middle of Hudson, Venus In Furs is not only a great place for exploring the Catskills and the Hudson Valley, but it’s also a destination in its own right. Whether sinking into the plush Chesterfield, or spending long evenings around the fire pit, you have plenty of options when it comes to relaxation. There’s a serious kitchen as well as a grill, but if you aren’t feeling like cooking yourself, the restaurants start from about a block away, while you can also reach the banks of the river in about ten minutes on foot.

Venus In Furs

Exercise Equipment

Courtyard

Set between the Hudson River and the Catskill Mountains, this spectacular 18th-century farmhouse is full of upstate New York charm. Nestled in 35 acres of secluded woodland, the house is a breath of fresh air less than two hours’ drive from the hustle and bustle of Manhattan. Step inside and you will instantly notice the owners’ keen aesthetic eye and attention to detail. Each room is bursting with character, and full of antique furniture, contemporary art, and vintage trinkets.  

The distinctive living room has a large wood burning fireplace and plenty of games for the kids. There is also a sun room which is perfect for relaxing in with a book. The farmhouse kitchen is well equipped with a range of appliances and cooking essentials. Upstairs, the palatial main suite comes with an office for remote working, a living area with its own fireplace and coffee station, and a claw-footed bathtub in the bathroom. The second and third bedroom have their own unique charm, and there is also a junior bedroom with plenty of toys and books for the little ones.

Outside, there is plenty to do and see. You can pick apples in autumn from your woodland (there are wellies at the house if it’s muddy!), go skiing and sledding in winter, or follow one of the nature trails leading to the creek. The village of Saugerties is a six-minute drive away, where you’ll find a grocery store, a farmer’s market and some laid back restaurants. 

The Dutch Farmhouse

Safe

What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock. Keen skiers will love staying here thanks to its close proximity to the Hunter ski centre, a 30-minute drive away. Discover the hidden lakes and waterfalls nearby by day, and stargaze from your own hammock by night. By the time you leave, you'll be at one with the woods. 

Soul Of The Willow

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866,  is steeped in history and rural charm. Full of wooden touches and warm accents, the home has been thoughtfully designed for relaxed, rural living. When you sip your morning coffee, you’ll have views of horses in the rolling fields. Later on, gather the group for meals by the traditional wood-burning stove between walks along the brooks and journeys into Wahconah Falls State Park. The home is secluded enough to let you disconnect surrounded by natural splendour, but there’s no shortage of entertainment to be found. Famous for its culture just as much as its landscape, The Berkshires are just as robust with art exhibitions and literary events as they are with rolling hills. Even Moby Dick is said to have been written somewhere amidst these very mountains. If you’re looking for a place on the east coast where the famous goes to truly hide, this is it. 


River Song

Games Room

Changing Table

Tucked away just outside of Woodstock, this impressive home welcomes families and friends to spend a few relaxing days in the Hudson Valley. Fully renovated in 2017, your hosts have truly thought of everything to ensure anyone who stays here has a magical experience. The original home was built in the late nineteenth-century and much of its original character has been retained, while an extension was added in the 1980s that now houses the spacious kitchen, lounge and four large bedrooms. 

There’s a separate office for anyone that needs to get some work done while you’re here and the playroom, gaming area, jungle gym and bouncy house are sure to keep the kids occupied. For the adults, the outdoor hot tub, swimming pool, and fire pit are perfect accessories to help you wind down at the end of a long day.

Upstate Escape

This 150-year-old Hudson Valley farmhouse sits on 16 acres of land that includes an apple orchard. It’s an idyllic base for those seeking an escape to the peace of the Catskills – though the town of Windham is just a ten-minute drive. If you tire of hiking, biking and fishing, you can always indulge in a spot of antiquing. The home is owned by a former interiors editor, which explains why it looks like it’s come straight from the pages of a magazine – the rustic style is oh-so charming. The loft bedroom is best suited to older children who won’t mind the ladder or lack of privacy. 

The Architect's Gallery

The Willow’s Resting Place is a glorious villa nestled into the forestry hilltop, overlooking the marvelous Woodstock country. Plentiful floor-to-ceiling windows stream natural light into the house, while offering magnificent views of the surrounding area. An elegant interior is created with the plush pastel living room, homely white kitchen and simple wooden dining table. There is a cosy TV room with a rich leather sofa and a stone-walled fireplace, perfecting for relaxing in. The large bedrooms have comfortable, deluxe beds and luxurious en-suite bathrooms. Stepping outside, there is an idyllic deck overlooking the rolling mountain landscape. The alfresco dining area is perfect for coming together with friends or family with a view, while leisurely lounge chairs are there for you to laze around on beautiful summer days. The villa is located in the ideal spot to get the best of both worlds. You can take a short drive to the Overlook Mountain Trailhead for a day of hiking, or perhaps head into Woodstock to explore the legendary town. 

The Willow's Resting Place

Featuring a full wall of glass doors and floor-to-ceiling windows, Riverside Modern was designed to maximise its views and boy, are we loving it. Unsurprisingly, the home has been featured in multiple home style magazines, because no matter the season, we guarantee you’ll be blown away. The natural colours that surround this home make it an excellent choice for a summer, winter, spring or fall vacation. The sleek contemporary design affords guests the chance to enjoy a relaxing trip to the Hudson Valley within its minimalist interiors. With three-bedrooms, Riverside Modern can host up to eight guests and is just a two-and-a-half-hour drive from New York City or Boston. So pack your bags city folks, it’s time to reconnect with nature in a most impressive setting.

Riverside Modern

Set in the heart of downtown Hudson, this unique home is just a ten-minute walk from the river and around the corner from Warren Street. Whether you're after a peaceful riverside stroll or want to visit one of your host's favourite restaurants, it won't take long for you to get there. After exploring your new neighbourhood, you'll come back to an art-filled home where your attentive host has spared no effort in making it feel welcoming and personal. We love the multi-level porch, with so many cosy spots to enjoy your morning coffee and soak in the sunshine. On mild days, leave the doors open and feel a sweet breeze blowing softly through the house as you work at the antique desk or make afternoon tea in the charming blue kitchen. With a large backyard all for yourself, pick up some local produce on your way back from Warren Street and fire up the grill for a delicious home-cooked dinner under the stars.

Hanging Baskets

Foosball / Table Football

Ping Pong Table

Pool / Snooker Table

Steam Room

Printer

Ski Storage / Boot Room

Nature meets luxury at this stunning Berkshire Mountain retreat. Just twenty minutes from Great Barrington and with hiking trails all around, this home is an idyllic escape from the hustle and bustle. Set in 167 private acres, this home has everything you could wish for. Admire mountain views from the hot tub on the sun deck, unwind in the steam room, and enjoy a tipple from the main bedroom’s wine bar. Your host can arrange for a chef to whip up feasts in the chef’s kitchen and order custom kegs for the kegerator. The open-concept living areas – with floor-to-ceiling windows – make socialising a dream. This home is perfect for a large family gathering. 

The Berkshires Splendour

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